Oakland Vacations from $267
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Pittsburgh-Meadow Lands
Price was $353, price is now $267 per person
$267
per person
Feb 17 - Feb 20
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 reviews)
when I stayed the fire alarm went off twice very loud and happen early in morning when I only wanted to sleep in and also went off as we were checking into the hotel but over all very nice staff and hotel
Reviewed on Dec 8, 2025
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was $645, price is now $480 per person
$480
per person
Apr 2 - Apr 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Nice rooms, beautiful building, good value, great location.
Reviewed on Jan 4, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was $386, price is now $293 per person
$293
per person
Feb 17 - Feb 20
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
The room and staff were great, breakfast was good as well. Dinner wasn’t as good. A very walkable location!
Reviewed on Jan 12, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was $724, price is now $550 per person
$550
per person
Apr 2 - Apr 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.
Reviewed on Jan 10, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $158 total per night from Jan 18 to Jan 19
$158 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (570 reviews)
Clean room.
Reviewed on Jan 7, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Jan 22 to Jan 23
$214 total
Jan 22 - Jan 23
Total with taxes and fees
9.2/10 Wonderful! (735 reviews)
The room was clean. The staff was very helpful from the valet, to the concierge to the front desk. When we checked in there was an issue with our room which they promptly rectified. We also requested extra pillows and they brought is more than enough. And every time we stepped into the bottom floor ...
Reviewed on Jan 8, 2026
Residence Inn Pittsburgh Oakland/University Place
3341 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Feb 4 to Feb 5
$139 total
Feb 4 - Feb 5
Total with taxes and fees
9/10 Wonderful! (924 reviews)
Spacious room. It could sleep 7 if kids are younger.
Reviewed on Jan 6, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
$65
per adult
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$97
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
- Shadyside Vacations
- Clemente Museum
- Strip District Vacations
- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.